Imidazole → 2,5,7-Trimethyl-2-triethylsilanyloxymethyl-6-vinyl-indan-1-ol

HRID 473071노트

반응식

HRID 473071 반응식
[OH:1][CH2:2][C:3]1([CH3:17])[CH2:11][C:10]2[C:5](=[C:6]([CH3:15])[C:7]([CH:13]=[CH2:14])=[C:8]([CH3:12])[CH:9]=2)[CH:4]1[OH:16].N1C=CN=C1.[Si:23](Cl)([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25]>C(Cl)Cl.O>[CH3:17][C:3]1([CH2:2][O:1][Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:11][C:10]2[C:5](=[C:6]([CH3:15])[C:7]([CH:13]=[CH2:14])=[C:8]([CH3:12])[CH:9]=2)[CH:4]1[OH:16]

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 59415730HCID 59415730, 화합물

생성물 1

HCID 684751572,5,7-Trimethyl-2-triethylsilanyloxymethyl-6-vinyl-indan-1-ol수율 88%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To the stirred solution of starting material 7 (0.85 g, 3.66 mmol) in dry CH2Cl2 added Imidazole (0.5 g, 7.32 mmol) and TESCl (0.6 mL, 3.66 mmol) sequentially at 0° C. under argon atmosphere and stirred the reaction mixture at same temperature for 6 h. Then reaction mixture was diluted with H2O (10 mL) followed by extraction with CH2Cl2 (50 mL), brine (25 mL), dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography (SiO2, 5 to 10% EtOAc in petroleum ether eluant) gave pure compound 8 (0.85 g, 88%) as syrup.

후처리

  1. customThen reaction mixture
  2. extractionfollowed by extraction with CH2Cl2 (50 mL), brine (25 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (SiO2, 5 to 10% EtOAc in petroleum ether eluant)

출처 및 근거

ORD 기록
ord-16743c616dea49a9862844f9a4e5463c
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633252B2

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